Piperidine → HCID 23518811, compound

HRID 1836386Notes

Reaction equation

HRID 1836386 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[C:5]([CH:7]1[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]1)=[O:6].C1CCNCC1.[F:23][C:24]1[C:29]([C:30](Cl)=[O:31])=[C:28]([F:33])[C:27]([F:34])=[C:26]([F:35])[C:25]=1[F:36]>O1CCCC1>[F:23][C:24]1[C:25]([F:36])=[C:26]([F:35])[C:27]([F:34])=[C:28]([F:33])[C:29]=1[C:30]([NH:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[C:5]([CH:7]1[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12]1)=[O:6])=[O:31]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 75256Pentafluorobenzoyl chlorideHCID 101306514-[3-Aminobenzoyl]-1-methylpiperidine

Product 1

HCID 23518811HCID 23518811, compoundYield 107.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[3-aminobenzoyl]-1-methylpiperidine (25 mg, 0.115 mmol) and (piperidinomethyl)-polystyrene (100 mg, 0.260 mmol) in tetrahydrofuran (2 mL) was allowed to stand for 10 min. Pentafluorobenzoyl chloride (33 μL, 0.229 mmol) was added to the reaction mixture. The reaction mixture was mixed for 2 h at ambient temperature. The reaction mixture was filtered and the filter cake was rinsed with methanol. Glacial acetic acid (0.5 mL) was added to the filtrate solution and the solution was mixed. This mixture was poured over a Varian Mega Bond Elut™ strong cation exchange column. The column was rinsed with methanol to remove impurities, then treated with a 7M ammonia in methanol to elute the product from the column. The solvent was evaporated to give 51 mg (>100%) of the title compound.

Workup

  1. additionThe reaction mixture was mixed for 2 h at ambient temperature
  2. filtrationThe reaction mixture was filtered
  3. washthe filter cake was rinsed with methanol
  4. additionGlacial acetic acid (0.5 mL) was added to the filtrate solution
  5. additionthe solution was mixed
  6. additionThis mixture was poured over a Varian Mega Bond Elut™ strong cation exchange column
  7. washThe column was rinsed with methanol
  8. customto remove impurities
  9. additiontreated with a 7M ammonia in methanol
  10. washto elute the product from the column
  11. customThe solvent was evaporated

Sources & evidence

ORD record
ord-bb11148c5c8e4d92845b40e396470b33
Source dataset
uspto-grants-2004_08
Patent number
US06777428B1

Reaction notes

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